Vanessa Trump is allegedly putting pressure on Tiger Woods to propose sooner than later. An insider says Donald Trump Jr.’s ex-wife is ready to see a ring on her finger, but the 50-year-old golfer is still carrying a lot of baggage from his prior marriage to Elin Nordegren given all the mistakes he made. A prior source in June 2025, only a few months after the pair made their relationship public through an Instagram post, said that Woods already had plans to marry Vanessa Trump “fairly soon” at the time, but a proposal has yet to materialize.
Woods worried he won’t “succeed at marriage,” insider says
“It’s no secret that she wants to take things up a notch and have a ring on her finger,” said a source about Vanessa Trump and Tiger Woods to the National Enquirer. “There’s pressure to propose coming down on him for sure.”
However, according to the insider, Woods is allegedly frightened that he’s going to fail his second shot at marriage and still carries a lot of regrets about his extramarital affairs that destroyed his first marriage.
The source explained, “It’s been nearly twenty years since [Tiger] blew his marriage to Elin and to this day, he will admit that was the biggest fumble of his life. He doesn’t talk about it a lot but on the rare occasion he opens up, he admits the regret still weighs on him pretty heavily.”
Compared to Nordegren, who has since married retired NFL tight end Jordan Cameron and has had several children with him, it’s apparently been harder for Woods to move on.
“Tiger hasn’t been able to do the same, at least not until he met Vanessa,” the source continued. “They really seem like a great match.”
“The only question is whether he’ll fully be able to shake his baggage from his divorce. It’s not just regrets over tearing his family apart. He also worries that he won’t be able to succeed at marriage.”
That said, the insider says Tiger would be making a mistake if he doesn’t propose soon. “He’s going to have to face his fears and do it before too long if he’s going to keep her happy.”
In the meantime, Tiger Woods has been advising Kai Trump, Vanessa’s daughter, in her debut on the LPGA Tour.
